Rare Finds and Fun Times at the Randolph Street Market Festival
How the Chicago festival became a can’t-miss antique and vintage destination.
Alongside the multiple sports stadiums, hundreds of skyscrapers, and what may be a seemingly endless supply of hot dog stands, the city of Chicago is also a premier destination in the Midwest for vintage and antique shopping. But within this vast number of retail choices available in the city’s 234 square miles, there is an event that takes place on West Randolph Street in the West Loop neighborhood that is on every Chicago-area vintage and antique collector’s calendar: the Randolph Street Market Festival.
The festival occurs twice a year in the spring and fall and claims to be America’s largest (and liveliest) urban antiques market. This appears to be true, at least at the recent indoor-outdoor event held on September 27–28, 2025, at the Chicago Plumbers Union Hall. As the music of a live band and DJ played, thousands of attendees shopped the hundreds of vendor tables, which sold handmade, vintage, and/or antique goods. For sale included shining household silver, glittering vintage fashions, sturdy mid-century furniture, and pristine original advertising signs. Food trucks and drink stalls kept shoppers satiated, and even a sentimental moment could be had with the “Poems While You Wait” table, which offered an original poem for a $10 donation to Rose Metal Press. There was even some friendly competition, as vendors throughout the space displayed neon green “Randolph Street Market Fave Finds” ribbons that were awarded by design experts.
“I think what makes the Randolph Street Market so special is that even though it’s big, it has a very intimate feeling,” explains Sally Schwartz, who founded the festival and runs it through her event planning company, Image Pilots. “I am very careful about which dealers I place next to each other. I look at the whole thing as a big seating chart for a party and try and fluff up the personality of every corner of the show.”
Sally began the event in 2003 as a strictly antiques market under the name Chicago Antique Market. It then evolved to the Randolph Street Market after being commonly referred to by visitors as the market on Randolph Street. Over the years, she also redesigned the event to have a festival feel by incorporating music and food. “I think of it as a cruise ship,” says Sally. “I want to keep people at the market all day. The event has become a real incubator for small artisanal foods.”
What has also grown is the festival’s consumer base, which has become more diverse in age over the last ten years. “The audience has definitely skewed younger and younger, and the older customers continue to come because once it’s in your blood, you never stop coming.”
Since 2003, Sally has watched some of her customers literally grow up, going from babies in strollers to attending the event while in college or as young adults. “That’s a really good feeling to know that this experience is deeply embedded in the nostalgia of so many of our customers today.”
Alongside the Randolph Street Market, Sally and Image Pilots now produce multiple retail festivals throughout the year in neighborhoods and suburbs across Chicago. The size of the shows can vary from 125 to 250 dealers, as do the themes, which may focus on antiques, contemporary vintage, and/or holiday decor.
Upcoming events include the Modern Vintage Chicago Fashion & Home event on October 5 in the neighborhood of Ravenswood that will feature contemporary decor and clothing, and the Randolph Holiday Markets on November 15–16 and December 13–14, both held at the Chicago Plumbers Union Hall, in which vendors will sell festive goods for the upcoming holiday season.
“I personally think the market just gets better and better,” says Sally. “It’s like Darwin’s theory, you have to be the best at what you do to survive, and these dealers are warriors. Their eye gets better, their displays get better, and the customers get better at appreciating the dealers and their wares, which just creates even more momentum. They’re creating new memories together.”
Visit randolphstreetmarket.com for more information.
All photographs are courtesy of Kaybrophoto.
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